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EP4559995A1 - Amine compounds as antiwear agents - Google Patents

Amine compounds as antiwear agents Download PDF

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Publication number
EP4559995A1
EP4559995A1 EP23307044.0A EP23307044A EP4559995A1 EP 4559995 A1 EP4559995 A1 EP 4559995A1 EP 23307044 A EP23307044 A EP 23307044A EP 4559995 A1 EP4559995 A1 EP 4559995A1
Authority
EP
European Patent Office
Prior art keywords
group
amine compound
formula
lubricant composition
mixtures
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23307044.0A
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German (de)
French (fr)
Inventor
Pankaj Chakraborty
Mahesh Kadam
Goulven BOUVIER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
TotalEnergies Onetech SAS
Original Assignee
TotalEnergies Onetech SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by TotalEnergies Onetech SAS filed Critical TotalEnergies Onetech SAS
Priority to EP23307044.0A priority Critical patent/EP4559995A1/en
Priority to PCT/EP2024/083261 priority patent/WO2025109151A1/en
Publication of EP4559995A1 publication Critical patent/EP4559995A1/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102Aliphatic fractions
    • C10M2203/1025Aliphatic fractions used as base material
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02Pour-point; Viscosity index
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/04Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/25Internal-combustion engines

Definitions

  • the present invention concerns amine compounds as antiwear agents in lubricant compositions.
  • Lubricating compositions also called “lubricants” are commonly used in engines for the main purpose of reducing the friction forces between the various metal parts in motion in engines. They are also effective in preventing premature wear or even damage to these parts, and in particular to their surfaces.
  • a lubricant composition is typically composed of a base oil with which several additives are generally associated, dedicated to stimulate the lubricating performances of the base oil, but also to provide additional performances.
  • antiwear additives additives known as "antiwear” additives are contemplated in order to reduce the wear of the components in the propulsion system, especially of the mechanical components of the motor, and thereby to prevent deterioration in the durability of the motor.
  • antiwear additives examples including dimercaptothiadiazoles, polysulfides, especially sulfur-containing olefins, amine phosphates, or else phosphosulfur additives, such as metal alkylthiophosphates, more particularly zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • antiwear additives presently employed in lubricants for vehicle motors such as dimercaptothiadiazoles, zinc dithiophosphate or else polysulfides, have the disadvantage, unfortunately, of being corrosive.
  • motorcycle engine oil lubricates both engine and transmission part.
  • the friction plate rubs with the clutch hub which is made of aluminum.
  • higher aluminum wear is observed in case of motorcycle engine oil.
  • the aim of the present invention is thus to provide an antiwear agent, especially for improving the aluminum wear.
  • the aim of the present invention is also to provide an improved method for reducing aluminum wear in particular for motorcycle engine.
  • the present invention relates to the use of at least one amine compound as antiwear agent in a lubricant composition comprising at least one base oil, wherein said amine compound is selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  • the lubricant composition comprises at least one base oil and a specific antiwear agent chosen from amine compounds.
  • the amine compounds used according to the invention are selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  • Ethoxylated tallow amines are ethoxylated amines derived from tallow oil.
  • Alkyl triamines are for example triamines bearing three (C 1 -C 20 )alkyl groups.
  • the antiwear agent according to the invention is advantageous in that it allows in particular to reduce the aluminum loss during the use of the engine, in particular of the motorcycle engine.
  • the amine compound used as antiwear agent is a compound having the formula (I), or a mixture of different compounds having the formula (I): wherein:
  • C t -C z means a carbon-based chain which can have from t to z carbon atoms, for example C 1 -C 3 means a carbon-based chain which can have from 1 to 3 carbon atoms.
  • an alkyl group means: a linear or branched, saturated, hydrocarbon-based aliphatic group.
  • alkenyl refers to a branched or straight-chain monovalent unsaturated aliphatic hydrocarbon group having one or more carbon double bonds.
  • the antiwear agent according to the invention is either a compound of formula (I) as defined above, or a mixture of several compounds of formula (I) as defined above.
  • the amine compound used as antiwear agent within the present invention is a compound having the formula (1-1), or a mixture of different compounds having the formula (I-1):
  • R being selected from the group consisting of: linear (C 16 -C 18 )alkyl groups, linear (C 16 -C 18 )alkenyl groups comprising one insaturation, linear (C 16 -C 18 )alkenyl groups comprising two insaturations, and mixtures thereof.
  • the antiwear agent according to the invention is either a compound of formula (I-1) as defined above, or a mixture of several compounds of formula (I-1) as defined above.
  • the amine compound used as antiwear agent is a mixture of different compounds having the formula (I-1).
  • Said mixture comprises for example two, three, four, five, or six different compounds of formula (I-1) as defined above. These compounds differ in the nature and/or size of the R group as defined above in formula (I-1).
  • the amine compound used as antiwear agent within the present invention is a compound having the formula (I-2), or a mixture of different compounds having the formula (I-2):
  • R being selected from the group consisting of: linear (C 16 -C 18 )alkyl groups, linear (C 16 -C 18 )alkenyl groups comprising one insaturation, and mixtures thereof.
  • the antiwear agent according to the invention is either a compound of formula (I-2) as defined above, or a mixture of several compounds of formula (I-2) as defined above.
  • the amine compound used as antiwear agent is a mixture of different compounds having the formula (I-2).
  • Said mixture comprises for example two, three, four, five, or six different compounds of formula (I-2) as defined above. These compounds differ in the nature and/or size of the R group as defined above in formula (I-2).
  • the amount of the amine compound used according to the invention is comprised from 0.01% to 5%, preferably from 0.02% to 1%, and more preferably from 0.02% to 0.5%, by weight in relation to the total weight of the lubricant composition.
  • the amount of the amine compound of formula (I-1) used according to the invention is comprised from 0.01% to 0.5%, preferably from 0.02% to 0.03%, by weight in relation to the total weight of the lubricant composition.
  • the amount of the amine compound of formula (I-2) used according to the invention is comprised from 0.01% to 2%, preferably from 0.1% to 1%, by weight in relation to the total weight of the lubricant composition.
  • the lubricant composition used within the present invention also comprises a base oil.
  • a lubricant composition as considered according to the invention more particularly comprises one or more base oils and, optionally, other additives conventionally considered in lubricant compositions.
  • a lubricant composition comprises one or more base oils.
  • base oils may be selected from base oils conventionally used in the field of lubricant oils, such as mineral, synthetic or natural, animal or vegetable oils or mixtures thereof.
  • It may be a mixture of several base oils, for example a mixture of two, three or four base oils.
  • the base oils of the lubricant compositions according to the invention may in particular be oils of mineral or synthetic origin belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in Table 1 below or mixtures thereof.
  • Table 1 Content of saturated compounds Sulphur content Viscosity index (VI) Group I Mineral oils ⁇ 90% > 0.03% 80 ⁇ VI ⁇ 120 Group II Hydrocracked oils ⁇ 90% ⁇ 0.03% 80 ⁇ VI ⁇ 120 Group III Hydro-isomerized oils ⁇ 90% ⁇ 0.03% 80 ⁇ VI ⁇ 120 Group IV Polyalphaolefins (PAO) Group V Esters and other bases not included in groups I to IV
  • Synthetic base oils can be esters of carboxylic acids and alcohols, polyalphaolefins or polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms.
  • the polyalphaolefins used as base oils are for example obtained from monomers comprising 4 to 32 carbon atoms, for example from decene, octene or dodecene, and whose viscosity at 100°C is between 1.5 and 15 mm 2 .s-1 according to ASTM D445. Their average molecular weight is generally between 250 and 3000 according to ASTM D5296.
  • Mixtures of synthetic and mineral oils, which may be biobased, can also be used.
  • the lubricant composition under consideration according to the invention comprises at least one base oil selected from group II, III and IV oils of the API classification, and mixtures thereof.
  • the base oil is selected from the group consisting of: base oils of Group I, base oils of Group II, base oils of Group III, and mixtures thereof, and is preferably a mixture of two or three base oils.
  • the lubricant composition used within the invention comprises a mixture of two base oils, in particular of one base oil of Group I and one base oil of Group III.
  • the amount of base oil(s) is comprised from 70% to 90%, preferably from 75% to 85%, by weight in relation to the total weight of the lubricant composition.
  • the amount of base oil(s) of Group I is comprised from 5% to 30%, preferably from 10% to 20%, by weight in relation to the total weight of the lubricant composition.
  • the amount of base oil(s) of Group III is comprised from 40% to 80%, preferably from 50% to 70%, by weight in relation to the total weight of the lubricant composition.
  • a lubricant composition used according to the invention may comprise any type of additives suitable for the intended use of the lubricant, as detailed hereafter, for example for use in engine systems for light or heavy vehicles.
  • additives can be introduced alone and/or in the form of a mixture, or "additive package", like those already available for sale in commercial lubricant formulations for vehicle engines, with performance levels as defined by the ACEA ("Association des Constructeurs Eurofugs d'Automobiles” ) and/or the API (American Petroleum Institute), which are well known to the man of the trade.
  • ACEA Association des Constructeurs Eurofugs d'Automobiles
  • API American Petroleum Institute
  • the lubricant composition used according to the invention further comprises at least one additive selected from the group consisting of: friction modifying additives, anti-wear additives different from the anti-wear additive according to the invention, extreme pressure additives, antioxidants, viscosity index improvers, pour point depressant additives, dispersants, antifoam agents, thickeners, corrosion inhibitors, and mixtures thereof.
  • the lubricant composition used according to the invention further comprises at least one additive selected from the group consisting of: antioxidants, viscosity index improvers, pour point depressant additives, and mixtures thereof.
  • a lubricant composition used according to the invention may comprise at least one friction modifying additive.
  • the friction modifying additives may be selected from compounds providing metallic elements and ash-free compounds, preferably from ash-free compounds.
  • transition metal complexes such as Mo, Sb, Sn, Fe, Cu, Zn whose ligands may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
  • the friction-modifying additives are selected from ash-free compounds, generally of organic origin and which may be more particularly selected from monoesters of fatty acids and polyols, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, borate fatty epoxides, fatty amines or fatty acid glycerol esters.
  • the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
  • a lubricant composition comprises at least one friction-modifying additive, in particular molybdenum-based.
  • the molybdenum-based compounds may be selected from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and mixtures thereof.
  • a lubricant composition considered according to the invention may comprise from 0.01 to 5% by weight, preferably from 0.01 to 5% by weight, more preferably from 0.1 to 2% by weight or even more preferably from 0.1 to 1.5% by weight, based on the total weight of the lubricant composition, of friction modifying additives.
  • a lubricant composition according to the invention may comprise at least one anti-wear and/or extreme pressure additive.
  • Anti-wear additives and extreme pressure additives protect rubbing surfaces by forming a protective film adsorbed on these surfaces.
  • the anti-wear additives are selected from phospho-sulphur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • Preferred compounds are of the formula Zn((SP(S)(OR 3 )(OR 4 )) 2 , wherein R 3 and R 4 , which may be the same or different, independently represent an alkyl group, preferably an alkyl group having from 1 to 18 carbon atoms.
  • Amine phosphates are also anti-wear additives which can be employed in the lubricant composition according to the invention.
  • the phosphorus provided by these additives can act as a poison to automotive catalytic systems because these additives are ash generators.
  • These effects can be minimized by partially substituting the amine phosphates with additives that do not contribute phosphorus, such as, for example, polysulfides, in particular sulfur-containing olefins.
  • the extreme-pressure and/or anti-wear additive(s) may be present in a lubricant composition according to the invention in a content ranging from 0.01% to 6% by weight, preferably from 0.05% to 4% by weight, more preferably from 0.1% to 2% by weight relative to the total mass of lubricant composition.
  • a lubricant composition considered according to the invention may comprise at least one antioxidant additive.
  • the antioxidant additives are essentially dedicated to delaying the degradation of the lubricant composition in service. This degradation may result in particular in the formation of deposits, in the presence of sludge or in an increase in the viscosity of the lubricating composition. They act in particular as radical inhibitors or hydroperoxide destroyers.
  • antioxidant additives commonly used, we can mention the phenolic type antioxidant additives, the amino type antioxidant additives, the phosphosulphur antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can be ash generating. Phenolic antioxidant additives may be ashless or may be in the form of neutral or basic metal salts. In particular, the antioxidant additives may be selected from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C 1 -C 12 alkyl group, N,N'-dialkyl-aryl-diamines and mixtures thereof.
  • the sterically hindered phenols are selected from compounds comprising a phenol group in which at least one vicinal carbon of the carbon bearing the alcohol function is substituted by at least one C 1 -C 10 alkyl group, preferably a C 1 -C 6 alkyl group, preferably a C 4 alkyl group, preferably by the ter-butyl group.
  • Amino compounds are another class of antioxidant additives that can be used, optionally in combination with phenolic antioxidant additives.
  • amine compounds are aromatic amines, for example aromatic amines of the formula NR 5 R 6 R 7 wherein R 5 represents an aliphatic group or an aromatic group, optionally substituted, R 6 represents an aromatic group, optionally substituted, R 7 is a hydrogen atom, an alkyl group, an aryl group or a group of the formula R 8 S(O) z R 9 in which R 8 is an alkylene group or an alkenylene group, R 9 is an alkyl group, an alkenyl group or an aryl group and z is 0, 1 or 2. Sulfurized alkyl phenols or alkali and alkaline earth metal salts thereof may also be used as antioxidant additives.
  • a lubricant composition considered according to the invention may contain any type of antioxidant additives known to the skilled person.
  • the lubricant composition comprises at least one ash-free antioxidant additive.
  • a lubricant composition considered according to the invention may comprise from 0.1% to 2% by weight, relative to the total weight of the composition, of at least one antioxidant additive.
  • a lubricant composition used according to the invention may also comprise at least one viscosity index improver (VI).
  • Viscosity index improvers (VI) in particular viscosity index improver polymers, ensure good cold-holding properties and minimum viscosity at high temperatures.
  • viscosity index improvers examples include polymeric esters, hydrogenated or non-hydrogenated homopolymers or copolymers of styrene, butadiene and isoprene, olefin homopolymers or copolymers, such as ethylene or propylene, polyacrylates and polymethacrylates (PMA).
  • a lubricant composition used according to the invention comprises at least one viscosity index improver selected from linear, grafted, comb or star, preferably star, polymethacrylates (PMA) and hydrogenated polyisoprene-styrene (PISH).
  • a viscosity index improver selected from linear, grafted, comb or star, preferably star, polymethacrylates (PMA) and hydrogenated polyisoprene-styrene (PISH).
  • the viscosity index improving additive(s) may be present in a lubricant composition according to the invention in a content ranging from 1 to 20% by weight, in particular from 10 to 15% by weight, based on the total weight of the lubricant composition.
  • a lubricant composition according to the invention is free of viscosity index improving additive.
  • a lubricant composition used according to the invention may comprise at least one pour point depressant additive (also known as "PPD" agents).
  • pour point depressant additives include alkyl polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes and alkylated polystyrenes.
  • the pour point depressant additive(s) may be present in a lubricant composition according to the invention in a content ranging from 0.01% to 1% by weight, in particular from 0.1% to 0.5% by weight, based on the total weight of the lubricant composition.
  • a lubricating composition used according to the invention may also include at least one dispersing agent.
  • the dispersing agents ensure the suspension and removal of insoluble solid contaminants consisting of oxidation by-products that are formed when the lubricant composition is in use. They may be selected from Mannich bases, succinimides and derivatives thereof.
  • a lubricant composition considered according to the invention may comprise from 0.2% to 10% by weight of dispersing agent(s), based on the total weight of the composition.
  • a lubricating composition used according to the invention may also comprise at least one antifoam additive.
  • the antifoam additives may be selected from polar polymers such as polymethylsiloxanes or polyacrylates.
  • a lubricant composition considered according to the invention may comprise from 0.01% to 3% by weight of antifoam additive(s), relative to the total weight of the lubricant composition.
  • the present invention also relates to the use as defined above, wherein the lubricant composition is intended for the lubrication of motorcycle engines.
  • the antiwear agent as defined above in particular having the formula (I), (I-1) or (I-2), is preferably used in lubricant compositions intended for the lubrication of motorcycle engines.
  • the present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  • the base oil is as defined above.
  • the antiwear agent is as defined above.
  • the amine compound is as defined above.
  • the present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being a compound having the formula (I), or mixtures of such compounds.
  • the present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being a compound having the formula (I-1), or mixtures of such compounds.
  • the present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being a compound having the formula (I-2), or mixtures of such compounds.
  • compositions are mentioned in table 2: CC CL1 CL2 Mixture of base oils 81.45 81.30 81.425 Additive package 18.25 18.25 18.25 PPD additive 0.2 0.2 0.2 Antioxidant 0.1 0.1 0.1 Compound of formula (I-2) - 0.15 Compound of formula (I-1) - 0.025
  • the additive package comprises in particular a dispersant, a detergent, an antioxidant, and/or an anti-foam additive.
  • the CAS number of the compound of formula (I-2) is 1219826-66-0 (and REACH number 01-2119487012-45-0000).
  • the CAS number of the compound of formula (I-1) is 1218787-32-6 (and REACH number 01-2119510877-33-0000).
  • the viscosity index (VI) is calculated from the measures of the kinematic viscosity at 40°C and 100°C. These values are then compared to the results of two reference oils. The calculation is made according to the ASTM D2270 standard.
  • CCS at -20°C is determined according to the ASTM D5293-20 standard.
  • LVFA test is used to evaluate the lubricant's frictional characteristics for clutch applications for motorcycle, Industrial, Off-Road and Marine Application.
  • Test Fluid temperature is indirectly controlled by heat medium oil and load is applied by servo actuator with hydraulic system, rotates the friction plate by servo motor via gearbox for high rigidity driveline.
  • LVFA method is designed to measure frictional characteristics in a continuously changing velocity.
  • the Al plate is made of Aluminium Alloy HE30/6082, composition is given below:
  • test conditions are as follows:

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Abstract

The present invention relates to the use of at least one amine compound as antiwear agent in a lubricant composition comprising at least one base oil, wherein said amine compound is selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.

Description

  • The present invention concerns amine compounds as antiwear agents in lubricant compositions.
  • Lubricating compositions, also called "lubricants", are commonly used in engines for the main purpose of reducing the friction forces between the various metal parts in motion in engines. They are also effective in preventing premature wear or even damage to these parts, and in particular to their surfaces.
  • For this purpose, a lubricant composition is typically composed of a base oil with which several additives are generally associated, dedicated to stimulate the lubricating performances of the base oil, but also to provide additional performances.
  • More particularly, additives known as "antiwear" additives are contemplated in order to reduce the wear of the components in the propulsion system, especially of the mechanical components of the motor, and thereby to prevent deterioration in the durability of the motor. There are a wide variety of antiwear additives, examples including dimercaptothiadiazoles, polysulfides, especially sulfur-containing olefins, amine phosphates, or else phosphosulfur additives, such as metal alkylthiophosphates, more particularly zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP.
  • The antiwear additives presently employed in lubricants for vehicle motors, such as dimercaptothiadiazoles, zinc dithiophosphate or else polysulfides, have the disadvantage, unfortunately, of being corrosive.
  • Unlike passenger car engine oil, motorcycle engine oil lubricates both engine and transmission part. In motorcycle clutch basket, the friction plate rubs with the clutch hub which is made of aluminum. Thus higher aluminum wear is observed in case of motorcycle engine oil.
  • Several products with variation of viscosity were already proposed but without any improvement of the aluminum wear.
  • The aim of the present invention is thus to provide an antiwear agent, especially for improving the aluminum wear.
  • The aim of the present invention is also to provide an improved method for reducing aluminum wear in particular for motorcycle engine.
  • Therefore, the present invention relates to the use of at least one amine compound as antiwear agent in a lubricant composition comprising at least one base oil, wherein said amine compound is selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  • In the use according the invention, the lubricant composition comprises at least one base oil and a specific antiwear agent chosen from amine compounds.
  • The amine compounds used according to the invention are selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  • Ethoxylated tallow amines are ethoxylated amines derived from tallow oil. Alkyl triamines are for example triamines bearing three (C1-C20)alkyl groups.
  • The antiwear agent according to the invention is advantageous in that it allows in particular to reduce the aluminum loss during the use of the engine, in particular of the motorcycle engine.
  • According to an embodiment, the amine compound used as antiwear agent is a compound having the formula (I), or a mixture of different compounds having the formula (I):
    Figure imgb0001
    wherein:
    • - R is a linear (C16-C18)alkyl group or a linear (C16-C18)alkenyl group, and
    • - R1 is a -(CH2)2-OH or a -(CH2)3-NH2 group.
  • Within the present invention, the expression "Ct-Cz" means a carbon-based chain which can have from t to z carbon atoms, for example C1-C3 means a carbon-based chain which can have from 1 to 3 carbon atoms.
  • Within the present invention, the term "an alkyl group" means: a linear or branched, saturated, hydrocarbon-based aliphatic group.
  • The term "alkenyl" refers to a branched or straight-chain monovalent unsaturated aliphatic hydrocarbon group having one or more carbon double bonds.
  • According to an embodiment, the antiwear agent according to the invention is either a compound of formula (I) as defined above, or a mixture of several compounds of formula (I) as defined above.
  • According to an embodiment, the amine compound used as antiwear agent within the present invention is a compound having the formula (1-1), or a mixture of different compounds having the formula (I-1):
    Figure imgb0002
  • R being selected from the group consisting of: linear (C16-C18)alkyl groups, linear (C16-C18)alkenyl groups comprising one insaturation, linear (C16-C18)alkenyl groups comprising two insaturations, and mixtures thereof.
  • According to an embodiment, the antiwear agent according to the invention is either a compound of formula (I-1) as defined above, or a mixture of several compounds of formula (I-1) as defined above.
  • Preferably, in formula (I-1), R is selected from the group consisting of: -(CH2)15-CH3, -(CH2)16-CH3, -(CH2)17-CH3, -(CH2)8-CH=CH-(CH2)7-CH3, -(CH2)8-CH=CH-(CH2)5-CH3, -(CH2)8-CH=CH-CH2-CH=CH-(CH2)4-CH3, and mixtures thereof.
  • According to a preferred embodiment, the amine compound used as antiwear agent is a mixture of different compounds having the formula (I-1). Said mixture comprises for example two, three, four, five, or six different compounds of formula (I-1) as defined above. These compounds differ in the nature and/or size of the R group as defined above in formula (I-1).
  • According to an embodiment, the amine compound used as antiwear agent within the present invention is a compound having the formula (I-2), or a mixture of different compounds having the formula (I-2):
    Figure imgb0003
  • R being selected from the group consisting of: linear (C16-C18)alkyl groups, linear (C16-C18)alkenyl groups comprising one insaturation, and mixtures thereof.
  • According to an embodiment, the antiwear agent according to the invention is either a compound of formula (I-2) as defined above, or a mixture of several compounds of formula (I-2) as defined above.
  • Preferably, in formula (I-2), R is selected from the group consisting of: -(CH2)15-CH3, -(CH2)16-CH3, -(CH2)17-CH3, -(CH2)8-CH=CH-(CH2)7-CH3, -(CH2)8-CH=CH-(CH2)5-CH3, and mixtures thereof.
  • According to a preferred embodiment, the amine compound used as antiwear agent is a mixture of different compounds having the formula (I-2). Said mixture comprises for example two, three, four, five, or six different compounds of formula (I-2) as defined above. These compounds differ in the nature and/or size of the R group as defined above in formula (I-2).
  • According to an embodiment, the amount of the amine compound used according to the invention is comprised from 0.01% to 5%, preferably from 0.02% to 1%, and more preferably from 0.02% to 0.5%, by weight in relation to the total weight of the lubricant composition.
  • According to an embodiment, the amount of the amine compound of formula (I-1) used according to the invention is comprised from 0.01% to 0.5%, preferably from 0.02% to 0.03%, by weight in relation to the total weight of the lubricant composition.
  • According to an embodiment, the amount of the amine compound of formula (I-2) used according to the invention is comprised from 0.01% to 2%, preferably from 0.1% to 1%, by weight in relation to the total weight of the lubricant composition.
  • As mentioned above, the lubricant composition used within the present invention also comprises a base oil.
  • A lubricant composition as considered according to the invention more particularly comprises one or more base oils and, optionally, other additives conventionally considered in lubricant compositions.
  • Conventionally, a lubricant composition comprises one or more base oils.
  • These base oils may be selected from base oils conventionally used in the field of lubricant oils, such as mineral, synthetic or natural, animal or vegetable oils or mixtures thereof.
  • It may be a mixture of several base oils, for example a mixture of two, three or four base oils.
  • The base oils of the lubricant compositions according to the invention may in particular be oils of mineral or synthetic origin belonging to groups I to V according to the classes defined in the API classification (or their equivalents according to the ATIEL classification) and presented in Table 1 below or mixtures thereof. Table 1
    Content of saturated compounds Sulphur content Viscosity index (VI)
    Group I Mineral oils < 90% > 0.03% 80 ≤ VI < 120
    Group II Hydrocracked oils ≥ 90% ≤ 0.03% 80 ≤ VI < 120
    Group III Hydro-isomerized oils ≥ 90% ≤ 0.03% 80 ≤ VI < 120
    Group IV Polyalphaolefins (PAO)
    Group V Esters and other bases not included in groups I to IV
  • Mineral base oils include all types of base oils obtained by atmospheric and vacuum distillation of crude oil, followed by refining operations such as solvent extraction, de-alkalization, solvent dewaxing, hydrotreating, hydrocracking, hydroisomerization and hydrofining.
  • Synthetic base oils can be esters of carboxylic acids and alcohols, polyalphaolefins or polyalkylene glycol (PAG) obtained by polymerization or copolymerization of alkylene oxides comprising from 2 to 8 carbon atoms, in particular from 2 to 4 carbon atoms. The polyalphaolefins used as base oils are for example obtained from monomers comprising 4 to 32 carbon atoms, for example from decene, octene or dodecene, and whose viscosity at 100°C is between 1.5 and 15 mm2.s-1 according to ASTM D445. Their average molecular weight is generally between 250 and 3000 according to ASTM D5296.
  • Mixtures of synthetic and mineral oils, which may be biobased, can also be used.
  • There is generally no limitation on the use of different base oils in the lubricant composition, except that they must have properties, such as viscosity, viscosity index, sulfur content, or oxidation resistance, suitable for use in engine systems, especially vehicle engines.
  • Preferably, the lubricant composition under consideration according to the invention comprises at least one base oil selected from group II, III and IV oils of the API classification, and mixtures thereof.
  • According to one embodiment, the base oil is selected from the group consisting of: base oils of Group I, base oils of Group II, base oils of Group III, and mixtures thereof, and is preferably a mixture of two or three base oils.
  • Preferably, the lubricant composition used within the invention comprises a mixture of two base oils, in particular of one base oil of Group I and one base oil of Group III.
  • According to an embodiment, the amount of base oil(s) is comprised from 70% to 90%, preferably from 75% to 85%, by weight in relation to the total weight of the lubricant composition.
  • According to an embodiment, the amount of base oil(s) of Group I is comprised from 5% to 30%, preferably from 10% to 20%, by weight in relation to the total weight of the lubricant composition.
  • According to an embodiment, the amount of base oil(s) of Group III is comprised from 40% to 80%, preferably from 50% to 70%, by weight in relation to the total weight of the lubricant composition.
  • A lubricant composition used according to the invention may comprise any type of additives suitable for the intended use of the lubricant, as detailed hereafter, for example for use in engine systems for light or heavy vehicles.
  • These additives can be introduced alone and/or in the form of a mixture, or "additive package", like those already available for sale in commercial lubricant formulations for vehicle engines, with performance levels as defined by the ACEA ("Association des Constructeurs Européens d'Automobiles") and/or the API (American Petroleum Institute), which are well known to the man of the trade.
  • According to an embodiment, the lubricant composition used according to the invention further comprises at least one additive selected from the group consisting of: friction modifying additives, anti-wear additives different from the anti-wear additive according to the invention, extreme pressure additives, antioxidants, viscosity index improvers, pour point depressant additives, dispersants, antifoam agents, thickeners, corrosion inhibitors, and mixtures thereof.
  • According to an embodiment, the lubricant composition used according to the invention further comprises at least one additive selected from the group consisting of: antioxidants, viscosity index improvers, pour point depressant additives, and mixtures thereof.
  • A lubricant composition used according to the invention may comprise at least one friction modifying additive.
  • The friction modifying additives may be selected from compounds providing metallic elements and ash-free compounds, preferably from ash-free compounds.
  • Among the compounds providing metallic elements, mention may be made of transition metal complexes such as Mo, Sb, Sn, Fe, Cu, Zn whose ligands may be hydrocarbon compounds comprising oxygen, nitrogen, sulfur or phosphorus atoms.
  • Advantageously, the friction-modifying additives are selected from ash-free compounds, generally of organic origin and which may be more particularly selected from monoesters of fatty acids and polyols, alkoxylated amines, alkoxylated fatty amines, fatty epoxides, borate fatty epoxides, fatty amines or fatty acid glycerol esters. According to the invention, the fatty compounds comprise at least one hydrocarbon group comprising from 10 to 24 carbon atoms.
  • According to an advantageous embodiment, a lubricant composition comprises at least one friction-modifying additive, in particular molybdenum-based.
  • In particular, the molybdenum-based compounds may be selected from molybdenum dithiocarbamates (Mo-DTC), molybdenum dithiophosphates (Mo-DTP), and mixtures thereof.
  • Advantageously, a lubricant composition considered according to the invention may comprise from 0.01 to 5% by weight, preferably from 0.01 to 5% by weight, more preferably from 0.1 to 2% by weight or even more preferably from 0.1 to 1.5% by weight, based on the total weight of the lubricant composition, of friction modifying additives.
  • A lubricant composition according to the invention may comprise at least one anti-wear and/or extreme pressure additive.
  • Anti-wear additives and extreme pressure additives protect rubbing surfaces by forming a protective film adsorbed on these surfaces.
  • There is a wide variety of anti-wear additives. Preferably for the lubricant composition according to the invention, the anti-wear additives are selected from phospho-sulphur additives such as metal alkylthiophosphates, in particular zinc alkylthiophosphates, and more specifically zinc dialkyldithiophosphates or ZnDTP. Preferred compounds are of the formula Zn((SP(S)(OR3)(OR4))2, wherein R3 and R4, which may be the same or different, independently represent an alkyl group, preferably an alkyl group having from 1 to 18 carbon atoms.
  • Amine phosphates are also anti-wear additives which can be employed in the lubricant composition according to the invention. However, the phosphorus provided by these additives can act as a poison to automotive catalytic systems because these additives are ash generators. These effects can be minimized by partially substituting the amine phosphates with additives that do not contribute phosphorus, such as, for example, polysulfides, in particular sulfur-containing olefins. Advantageously, the extreme-pressure and/or anti-wear additive(s) may be present in a lubricant composition according to the invention in a content ranging from 0.01% to 6% by weight, preferably from 0.05% to 4% by weight, more preferably from 0.1% to 2% by weight relative to the total mass of lubricant composition.
  • A lubricant composition considered according to the invention may comprise at least one antioxidant additive. The antioxidant additives are essentially dedicated to delaying the degradation of the lubricant composition in service. This degradation may result in particular in the formation of deposits, in the presence of sludge or in an increase in the viscosity of the lubricating composition. They act in particular as radical inhibitors or hydroperoxide destroyers.
  • Among the antioxidant additives commonly used, we can mention the phenolic type antioxidant additives, the amino type antioxidant additives, the phosphosulphur antioxidant additives. Some of these antioxidant additives, for example phosphosulfur antioxidant additives, can be ash generating. Phenolic antioxidant additives may be ashless or may be in the form of neutral or basic metal salts. In particular, the antioxidant additives may be selected from sterically hindered phenols, sterically hindered phenol esters and sterically hindered phenols comprising a thioether bridge, diphenylamines, diphenylamines substituted with at least one C1-C12 alkyl group, N,N'-dialkyl-aryl-diamines and mixtures thereof.
  • Preferably, the sterically hindered phenols are selected from compounds comprising a phenol group in which at least one vicinal carbon of the carbon bearing the alcohol function is substituted by at least one C1-C10 alkyl group, preferably a C1-C6 alkyl group, preferably a C4 alkyl group, preferably by the ter-butyl group.
  • Amino compounds are another class of antioxidant additives that can be used, optionally in combination with phenolic antioxidant additives. Examples of amine compounds are aromatic amines, for example aromatic amines of the formula NR5R6R7 wherein R5 represents an aliphatic group or an aromatic group, optionally substituted, R6 represents an aromatic group, optionally substituted, R7 is a hydrogen atom, an alkyl group, an aryl group or a group of the formula R8S(O)zR9 in which R8 is an alkylene group or an alkenylene group, R9 is an alkyl group, an alkenyl group or an aryl group and z is 0, 1 or 2. Sulfurized alkyl phenols or alkali and alkaline earth metal salts thereof may also be used as antioxidant additives.
  • A lubricant composition considered according to the invention may contain any type of antioxidant additives known to the skilled person. Advantageously, the lubricant composition comprises at least one ash-free antioxidant additive.
  • Also advantageously, a lubricant composition considered according to the invention may comprise from 0.1% to 2% by weight, relative to the total weight of the composition, of at least one antioxidant additive.
  • A lubricant composition used according to the invention may also comprise at least one viscosity index improver (VI). Viscosity index improvers (VI), in particular viscosity index improver polymers, ensure good cold-holding properties and minimum viscosity at high temperatures.
  • Examples of viscosity index improvers include polymeric esters, hydrogenated or non-hydrogenated homopolymers or copolymers of styrene, butadiene and isoprene, olefin homopolymers or copolymers, such as ethylene or propylene, polyacrylates and polymethacrylates (PMA).
  • Advantageously, a lubricant composition used according to the invention comprises at least one viscosity index improver selected from linear, grafted, comb or star, preferably star, polymethacrylates (PMA) and hydrogenated polyisoprene-styrene (PISH).
  • In particular, the viscosity index improving additive(s) may be present in a lubricant composition according to the invention in a content ranging from 1 to 20% by weight, in particular from 10 to 15% by weight, based on the total weight of the lubricant composition.
  • According to one embodiment, a lubricant composition according to the invention is free of viscosity index improving additive.
  • A lubricant composition used according to the invention may comprise at least one pour point depressant additive (also known as "PPD" agents). By slowing down the formation of kerosene crystals, pour point depressant additives generally improve the cold behavior of the lubricant composition. Examples of pour point depressants include alkyl polymethacrylates, polyacrylates, polyarylamides, polyalkylphenols, polyalkylnaphthalenes and alkylated polystyrenes.
  • In particular, the pour point depressant additive(s) may be present in a lubricant composition according to the invention in a content ranging from 0.01% to 1% by weight, in particular from 0.1% to 0.5% by weight, based on the total weight of the lubricant composition.
  • A lubricating composition used according to the invention may also include at least one dispersing agent. The dispersing agents ensure the suspension and removal of insoluble solid contaminants consisting of oxidation by-products that are formed when the lubricant composition is in use. They may be selected from Mannich bases, succinimides and derivatives thereof.
  • In particular, a lubricant composition considered according to the invention may comprise from 0.2% to 10% by weight of dispersing agent(s), based on the total weight of the composition.
  • A lubricating composition used according to the invention may also comprise at least one antifoam additive. The antifoam additives may be selected from polar polymers such as polymethylsiloxanes or polyacrylates.
  • In particular, a lubricant composition considered according to the invention may comprise from 0.01% to 3% by weight of antifoam additive(s), relative to the total weight of the lubricant composition.
  • As mentioned above, all of the additives detailed above can be introduced in the form of a mixture or "package" of additives.
  • According to this embodiment, the additive package may represent from 1% to 30% by mass with respect to the total mass of the composition, in particular from 1% to 20% by mass.
  • The present invention also relates to the use as defined above, wherein the lubricant composition is intended for the lubrication of motorcycle engines.
  • The antiwear agent as defined above, in particular having the formula (I), (I-1) or (I-2), is preferably used in lubricant compositions intended for the lubrication of motorcycle engines.
  • The present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  • According to an embodiment, the base oil is as defined above.
  • According to an embodiment, the antiwear agent is as defined above.
  • Preferably, in the method of the invention, the amine compound is as defined above.
  • The present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being a compound having the formula (I), or mixtures of such compounds.
  • The present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being a compound having the formula (I-1), or mixtures of such compounds.
  • The present invention also relates to a method for reducing aluminum wear for motorcycle engine, said method comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being a compound having the formula (I-2), or mixtures of such compounds.
  • EXAMPLES Example 1: Preparation of the lubricant compositions
  • The below lubricant compositions (CL compositions according to the invention and CC comparative composition) are prepared according to the usual protocols that are well-known from the skilled person.
  • The compositions are mentioned in table 2:
    CC CL1 CL2
    Mixture of base oils 81.45 81.30 81.425
    Additive package 18.25 18.25 18.25
    PPD additive 0.2 0.2 0.2
    Antioxidant 0.1 0.1 0.1
    Compound of formula (I-2) - 0.15
    Compound of formula (I-1) - 0.025
  • The additive package comprises in particular a dispersant, a detergent, an antioxidant, and/or an anti-foam additive.
  • The CAS number of the compound of formula (I-2) is 1219826-66-0 (and REACH number 01-2119487012-45-0000).
  • The CAS number of the compound of formula (I-1) is 1218787-32-6 (and REACH number 01-2119510877-33-0000).
  • The physicochemical parameters of the compositions are indicated in table 3, here below:
    CC CL1 CL2
    KV40 (mm2/s) 155.1 155.4 155.4
    KV100 (mm2/s) 20.45 20.37 20.37
    VI 155 152 152
    CCS @ -20°C 6574 6590 6590
    • KV40 is the kinematic viscosity at 40°C of the lubricant composition, that is measured according to the ASTM D445 standard.
    • KV100 is the kinematic viscosity at 100°C of the lubricant composition, that is measured according to the ASTM D445 standard.
  • The viscosity index (VI) is calculated from the measures of the kinematic viscosity at 40°C and 100°C. These values are then compared to the results of two reference oils. The calculation is made according to the ASTM D2270 standard.
  • CCS at -20°C is determined according to the ASTM D5293-20 standard.
  • Example 2: Evaluation of aluminum wear
  • This evaluation is made with the LVFA test (Low Velocity Friction Apparatus).
  • LVFA test is used to evaluate the lubricant's frictional characteristics for clutch applications for Motorcycle, Industrial, Off-Road and Marine Application.
  • It determines the friction coefficient between components in rotating-sliding contact at various speeds, loads, and temperatures. Test Fluid temperature is indirectly controlled by heat medium oil and load is applied by servo actuator with hydraulic system, rotates the friction plate by servo motor via gearbox for high rigidity driveline.
  • LVFA method is designed to measure frictional characteristics in a continuously changing velocity.
  • LVFA test was performed using the cellulose friction plate from Royal Enfield J Series engine and steel plate was replaced using aluminum plate which was prepared as per the dimension of the friction plate.
  • The Al plate is made of Aluminium Alloy HE30/6082, composition is given below:
    Figure imgb0004
  • The test conditions are as follows:
    • Temperature: 130°C
    • Surface Pressure: 0.5 Mpa
    • Sliding Speed: 1.0 m/s.
  • Weight of the aluminum plate was measured before and after the test, as mentioned in the below table:
    CC CL1 CL2
    Aluminium weight loss (mg) 54 26 13
  • It can thus be seen that the aluminum weight loss is strongly reduced with the compositions comprising the antiwear agent according to the invention, in comparison with the comparative composition (without any antiwear agent according to the invention).

Claims (13)

  1. The use of at least one amine compound as antiwear agent in a lubricant composition comprising at least one base oil, wherein said amine compound is selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  2. The use of claim 1, wherein the amine compound is a compound having the formula (I), or a mixture of different compounds having the formula (I):
    Figure imgb0005
    wherein:
    - R is a linear (C16-C18)alkyl group or a linear (C16-C18)alkenyl group, and
    - R1 is a -(CH2)2-OH or a -(CH2)3-NH2 group.
  3. The use of claim 1 or 2, wherein the amine compound is a compound having the formula (I-1), or a mixture of different compounds having the formula (I-1):
    Figure imgb0006
    R being selected from the group consisting of: linear (C16-C18)alkyl groups, linear (C16-C18)alkenyl groups comprising one insaturation, linear (C16-C18)alkenyl groups comprising two insaturations, and mixtures thereof.
  4. The use of claim 3, wherein R is selected from the group consisting of: -(CH2)15-CH3, -(CH2)16-CH3, -(CH2)17-CH3, -(CH2)8-CH=CH-(CH2)7-CH3, -(CH2)8-CH=CH-(CH2)5-CH3, -(CH2)8-CH=CH-CH2-CH=CH-(CH2)4-CH3, and mixtures thereof.
  5. The use of claim 3 or 4, wherein the amine compound is a mixture of different compounds having the formula (I-1).
  6. The use of claim 1 or 2, wherein the amine compound is a compound having the formula (I-2), or a mixture of different compounds having the formula (I-2):
    Figure imgb0007
    R being selected from the group consisting of: linear (C16-C18)alkyl groups, linear (C16-C18)alkenyl groups comprising one insaturation, and mixtures thereof.
  7. The use of claim 6, wherein R is selected from the group consisting of: -(CH2)15-CH3, -(CH2)16-CH3, -(CH2)17-CH3, -(CH2)8-CH=CH-(CH2)7-CH3, -(CH2)8-CH=CH-(CH2)5-CH3, and mixtures thereof.
  8. The use of claim 6 or 7, wherein the amine compound is a mixture of different compounds having the formula (I-2).
  9. The use of any one of claims 1 to 8, wherein the amount of the amine compound is comprised from 0.01% to 5%, preferably from 0.02% to 1%, and more preferably from 0.02% to 0.5%, by weight in relation to the total weight of the lubricant composition.
  10. The use of any one of claims 1 to 9, wherein the lubricant composition further comprises at least one additive selected from the group consisting of friction modifying additives, anti-wear additives different from the anti-wear compound as defined in any one of claims 1 to 9, extreme pressure additives, antioxidants, viscosity index improvers, pour point depressant additives, dispersants, antifoam agents, thickeners, corrosion inhibitors, and mixtures thereof.
  11. The use of any one of claims 1 to 10, wherein the lubricant composition is intended for the lubrication of motorcycle engines.
  12. A method for reducing aluminum wear for motorcycle engine comprising the lubrication of said motorcycle engine with a lubricant composition comprising at least one base oil and also comprising at least one amine compound as antiwear agent, said amine compound being selected from the group consisting of: ethoxylated tallow amines, alkyl triamines, and mixtures thereof.
  13. The method of claim 12, wherein the amine compound is as defined in any one of claims 2 to 8.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012087773A1 (en) * 2010-12-21 2012-06-28 The Lubrizol Corporation Lubricating composition containing an antiwear agent
US20160312144A1 (en) * 2013-12-17 2016-10-27 Total Marketing Services Lubricant composition based on fatty triamines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012087773A1 (en) * 2010-12-21 2012-06-28 The Lubrizol Corporation Lubricating composition containing an antiwear agent
US20160312144A1 (en) * 2013-12-17 2016-10-27 Total Marketing Services Lubricant composition based on fatty triamines

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
no. 1218787-32-6
OKUBO HIKARU ET AL: "Effects of concentration of zinc dialkyldithiophosphate on the tribological properties of tetrahedral amorphous carbon films in presence of organic friction modifiers", TRIBOLOGY INTERNATIONAL, vol. 94, 23 October 2015 (2015-10-23) - 23 October 2015 (2015-10-23), pages 446 - 457, XP029333735, ISSN: 0301-679X, DOI: 10.1016/J.TRIBOINT.2015.10.008 *

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